Random questions to ask: a free random question generator
Funny
What's the most random thing within arm's reach right now?
320 questions, all work-safe.
Good random questions to ask do one job: they get a person talking about something they didn't expect to talk about. The random question generator above draws from 320 questions written for mixed company, so they work with coworkers, clients, new friends and family at the same table. Pick a kind, press Next question, and copy the one you like into Slack or a text. 200 of them are printed below, sorted by kind.
20 random questions to ask anyone
Our favorites from every kind, mixed on purpose. If you only need one list, use this one.
- 1.What's the most random thing within arm's reach right now?
- 2.If you could see one statistic about your own life, what would you want to know?
- 3.Stairs or elevator?
- 4.What's a small decision that ended up changing your life?
- 5.Would you rather be the funniest person in the room or the best listener?
- 6.What job title would you invent for yourself?
- 7.Which household chore would you medal in if it were an Olympic sport?
- 8.If you found a door in your home you'd never noticed, what would you hope was behind it?
- 9.What's the best question anyone has ever asked you?
- 10.Follow the recipe or freestyle it?
- 11.Would you rather never wait in line again or never sit in traffic again?
- 12.Which work task secretly relaxes you?
- 13.What would a museum about your life sell in the gift shop?
- 14.If you could un-watch one film or show to see it fresh again, which one?
- 15.What's a book, film or song that found you at exactly the right time?
- 16.Scenic route or fastest route?
- 17.Would you rather have a pet dragon the size of a cat or a cat the size of a dragon?
- 18.What phrase from work has crept into your home life?
- 19.What trophy do you deserve that doesn't exist?
- 20.If you could send a one-line message to everyone on Earth, what would it say?
180 more random questions, sorted by kind
Thirty of each, so you can read down one list instead of rolling the dice.
30 funny and weird random questions
Odd on purpose. Good for a new group, a slow chat channel or the first minute of a call.
- 21.What's the oddest thing in your fridge right now?
- 22.If your morning had a movie title, what would it be?
- 23.What's a word you can never spell right on the first try?
- 24.Which vegetable do you trust the least?
- 25.What's the worst possible name for a cruise ship?
- 26.Which cartoon character would make the worst houseguest?
- 27.What phone number, other than your own, do you still know by heart?
- 28.If you were a friendly ghost, which building would you haunt?
- 29.What sandwich would you name after yourself, and what's in it?
- 30.Which animal do you think is secretly judging us?
- 31.What's the worst flavor idea for a toothpaste?
- 32.If you had a catchphrase, what would it be?
- 33.What would your stage name be if you joined the circus?
- 34.What's the most unusual thing you've ever found in a coat pocket?
- 35.Which piece of furniture best matches your personality?
- 36.What rule would you add to every elevator ride?
- 37.What's the funniest thing a kid has ever said to you?
- 38.If you could rename one day of the week, which one and to what?
- 39.What's one invention you'd happily un-invent?
- 40.What would you bring to a potluck if you never wanted to be invited back?
- 41.Which fruit has the best personality?
- 42.What's the longest you've searched for something that was already in your hand?
- 43.What's a totally normal thing that you find weirdly difficult?
- 44.If dogs ran the world, what's the first law they'd pass?
- 45.What song would you play to clear a room?
- 46.If you had to live inside one store for a week, which store?
- 47.What's the funniest misheard song lyric you've sung with confidence?
- 48.Which dinosaur would make the best apartment pet?
- 49.What's the weirdest compliment you've ever received?
- 50.What would you put on a billboard just to confuse people?
Want more like these? See our funny icebreaker questions.
30 deep random questions
Thoughtful without being heavy. Best with four to eight people who have already laughed together once.
- 51.Who believed in you before you believed in yourself?
- 52.What's something you're glad you didn't know in advance?
- 53.What does a really good conversation feel like to you?
- 54.What's a piece of advice you ignored and later wished you hadn't?
- 55.What's a place you return to when life gets loud?
- 56.What would you study if you went back to school just for fun?
- 57.Which year of your life taught you the most?
- 58.What's a compliment you find hard to accept?
- 59.What quality do you admire in others and wish you had more of?
- 60.What's a small thing a stranger did that you still remember?
- 61.What sound makes you feel at home?
- 62.What's something you hope never changes about you?
- 63.Which teacher do you still think about, and why?
- 64.What do you wish you'd started sooner?
- 65.What does being brave look like in everyday life?
- 66.Which chapter of your life would you title "The Plot Twist"?
- 67.What's a tradition you started yourself?
- 68.What's something simple the world could use more of?
- 69.What do people thank you for most often?
- 70.When do you lose track of time in a good way?
- 71.What would you tell a room of graduating students?
- 72.What's a kindness you'd like to pass on?
- 73.What did you believe about being an adult that turned out to be wrong?
- 74.What's the best mistake you ever made?
- 75.What part of your day would you never give up?
- 76.What's the last thing you made with your own hands?
- 77.What makes a place feel welcoming to you?
- 78.What's a lesson a child has taught you?
- 79.What's the most valuable thing you own that isn't worth much money?
- 80.What does a good listener do that most people don't?
30 random questions to ask coworkers
About how people work, not how well. Safe for a standup, a one-on-one or a new hire's first week.
- 81.What's the best work-related purchase you've ever made?
- 82.Which meeting do you wish could be a two-line message?
- 83.What's the most useful thing you've learned from a customer?
- 84.Which browser tab do you always have open?
- 85.What's the best "reply all" story you've witnessed?
- 86.What would you teach a new hire that isn't in the handbook?
- 87.What's your signature phrase in meetings?
- 88.What skill do you use at work that you learned somewhere unexpected?
- 89.What's the most creative fix you've seen for a work problem?
- 90.What kind of work makes the day fly by for you?
- 91.What's the strangest thing you've ever had to do for a job?
- 92.What would you put in a time capsule for this team?
- 93.What's a meeting you still talk about?
- 94.What does your ideal Friday afternoon at work look like?
- 95.Which tool did you resist at first and now can't work without?
- 96.What's your best trick for a 3 p.m. slump?
- 97.What's the most memorable team lunch you've ever had?
- 98.What did you think this job would be like before you started?
- 99.What's the oldest file on your desktop?
- 100.If our team had a trophy, what would it be for?
- 101.What's the best thing about your commute, or about not having one?
- 102.What job would you love to try for exactly one day?
- 103.What work habit did you pick up from a former boss or teammate?
- 104.How do you take notes: paper, app or memory?
- 105.What does our team do that other teams should steal?
- 106.What's the best out-of-office message you've seen?
- 107.What's your personal record for meetings in one day?
- 108.What's the most satisfying thing to cross off a to-do list?
- 109.What "boring" part of your job do you actually enjoy?
- 110.Which workplace buzzword would you retire forever?
Want more like these? See our check-in questions for team meetings.
30 hypothetical random questions
No right answer and no experience needed, so everyone in the room can play.
- 111.If you could have a lifetime supply of one thing, what would it be?
- 112.If you could add one room to your home with no budget, what would it be?
- 113.If you could live in any decade for a year, which would you choose?
- 114.If you had to eat at one restaurant for the rest of the year, which one?
- 115.If you could make one object in your home self-cleaning, what would it be?
- 116.If you had to teach a class of kids for a day, what would you teach?
- 117.If you were given a small island, what would you name it?
- 118.If you could bring back one extinct animal, which would it be?
- 119.If you had a time machine that only went forward, how far would you go?
- 120.If you could have any view from your window, what would you see?
- 121.If you had to change your first name, what would you pick?
- 122.If you could attend any event in the world next year, what would it be?
- 123.If you had to be an extra in any TV show, which would you pick?
- 124.If you could make one thing free for everyone, what would it be?
- 125.If you could design your own theme park ride, what would it be like?
- 126.If you had to wear one color for a year, which color?
- 127.If anyone, living or not, could cook you one meal, who's cooking?
- 128.If you could keep one kind of weather all year, what would it be?
- 129.If you could own any building in the world, which would it be?
- 130.If you could swap your commute for any transport, real or imaginary, what would you pick?
- 131.If you had to live on a boat, in a treehouse or in a lighthouse, which one?
- 132.If you could give every person one skill, what would it be?
- 133.If your town held a parade in your honor, what would be on the lead float?
- 134.If you could instantly finish one unfinished project, which one?
- 135.If you were stuck in an airport for 24 hours, how would you spend it?
- 136.If you could have any gadget from a movie, which would it be?
- 137.If you could open a museum about anything, what would it be about?
- 138.If you could only keep three apps on your phone, which three?
- 139.If you had to move to another planet, what would you bring from Earth?
- 140.If you could hear anyone's playlist, whose would you pick?
30 this or that random questions
Two options, one word. The fastest kind for a big meeting: everyone answers in the chat at once.
- 141.Podcast or playlist?
- 142.Breakfast or dinner?
- 143.Crunchy or smooth peanut butter?
- 144.Sticky notes or notes app?
- 145.Jigsaw puzzle or crossword?
- 146.Surprise party or planned party?
- 147.Dark mode or light mode?
- 148.Typing or handwriting?
- 149.Leftovers or something new?
- 150.Rain or snow?
- 151.Big party or small dinner?
- 152.Spicy or mild?
- 153.Bagel or croissant?
- 154.Lake or ocean?
- 155.Driver or passenger?
- 156.Cook or clean up?
- 157.Thriller or documentary?
- 158.Front row or back row?
- 159.Sparkling or still water?
- 160.Fireplace or campfire?
- 161.Farmers market or supermarket?
- 162.Soup or salad?
- 163.Roller coaster or Ferris wheel?
- 164.Zoo or aquarium?
- 165.Singing or dancing?
- 166.Trivia night or karaoke night?
- 167.New restaurant or old favorite?
- 168.Rewatch a favorite or start something new?
- 169.Subtitles on or off?
- 170.Bookstore or library?
Want more like these? See our this or that questions.
30 would you rather random questions
Pick a side, then defend it in one sentence. The defending is the fun part.
- 171.Would you rather have a rewind button or a fast-forward button for your day?
- 172.Would you rather always know what time it is or always know which way is north?
- 173.Would you rather live where it's always morning or always evening?
- 174.Would you rather have a garden that grows any food or a closet that makes any outfit?
- 175.Would you rather have free coffee for life or free lunch every Friday?
- 176.Would you rather speak in rhyme for a day or sing everything you say?
- 177.Would you rather have a desk by the window or a desk next to the snacks?
- 178.Would you rather explore a new city on foot or by bike?
- 179.Would you rather read the book first or watch the movie first?
- 180.Would you rather always find a parking spot or always get a green light?
- 181.Would you rather remember every name or every joke you hear?
- 182.Would you rather work from a treehouse or a houseboat?
- 183.Would you rather host the party or be the guest?
- 184.Would you rather live without a microwave or without a freezer?
- 185.Would you rather hold every meeting outdoors or cap every meeting at ten minutes?
- 186.Would you rather be great at every sport or every instrument?
- 187.Would you rather know every shortcut on your computer or every shortcut in your city?
- 188.Would you rather have a personal theme song or a personal mascot?
- 189.Would you rather only whisper or only shout for a day?
- 190.Would you rather take a class in something you love or something you've never tried?
- 191.Would you rather start work two hours earlier or finish two hours later?
- 192.Would you rather be able to pause a meeting or mute real life?
- 193.Would you rather visit every country once or one country every year for life?
- 194.Would you rather have the best seat at every concert or the best table at every restaurant?
- 195.Would you rather be stuck in an elevator with a great storyteller or a great singer?
- 196.Would you rather give up your phone's camera or its maps?
- 197.Would you rather get a snow day or a surprise sunny day off?
- 198.Would you rather live in a castle or a cabin in the woods?
- 199.Would you rather write a bestselling book or direct an award-winning film?
- 200.Would you rather get a handwritten letter or a surprise phone call?
Want more like these? See our would you rather questions.
Where to use random questions
The same question lands differently in a standup than at a dinner table. Here is where each kind works.
- Meeting openers. One question, one sentence each, before the agenda. On a big call, pick this or that so everyone can answer in the chat at once.
- One-on-ones. Open with a work or deep question instead of "how's it going?". One real answer tells you more than a status update.
- Road trips. Hypotheticals and would you rather questions can fill an hour, and the driver gets to play.
- Dinner and family gatherings. Pass one phone around the table. Each person draws a question for the person on their left.
- New groups and first days. Start with funny or this or that. Save the deep ones until people have laughed together once.
Posting in Slack or Teams every day? Our question of the day gives the whole team the same question each morning. For a first meeting with a new group, start from our icebreaker questions.
How to pick a good question for the room
A random question still needs one decision from you: is it right for these people, right now?
- Match the weight to the trust. New group: funny or this or that. A team that already knows each other: work or deep.
- Check that everyone can answer. A good question doesn't assume a pet, a partner, kids or a big travel budget. Every question here passes that test.
- Size the answer to the group. With twenty people, ask for one word. With four, ask for a story.
- Answer first. Your answer sets the length and the tone, and shows it's fine to be a little silly.
- Let people pass. Anyone can say "next" and draw another. Nobody owes the room an answer.
- Stop while it's fun. One question opens a meeting. Three make a game. Ten start to feel like a survey.
Want someone to run this for your team?
A random question fills five minutes. For a full hour where the whole team plays, a live host runs a show-and-tell scavenger hunt or a virtual game show on Zoom (Teams, Google Meet or Webex on request). Book about 2 weeks ahead, or get a free quote.
Two hosted games that get people talking, with today’s prices.
